The Generalist Edge

"Learn how to see. Realize that everything connects to everything else." – Leonardo da Vinci

1. Generalism is a mindset

When I started out as a Founders’ Associate, I didn’t know it was a crash course in generalism. It felt like chaos. Four years, different startups, and becoming Chief of Staff later, I realize the power of being a generalist is making the chaos work.

Generalism is not a career path. It could never be.

In a world which requires you to climb rigid ladders, generalists build webs across multiple disciplines. If there were a career path called “generalist”, it would be the opposite of what generalism embraces.

Generalism is a mindset requiring curiosity, adaptability, and connection.

At its core, generalism isn’t a role – it’s a holistic way of solving problems.

2. Curiosity is the best strategy

Having grown a community of hundreds of generalists, I’m often asked what to look for in a candidate for a generalist role.

Generalists embrace curiosity at all levels.

This can and will often include uncomfortable curiosity against the org’s will. Curiosity thrives in space – leaders must not only tolerate it but actively create room for it.

Questioning team members on their work culture inevitably led to resistance. Yet, those conversations led to critical operational improvements. That’s curiosity at work: it disrupts before it builds.

Curiosity is required at a macro and micro level. Micro curiosity means questioning assumptions causing day-to-day problems. Macro curiosity means zooming out to question the entire system built on these assumptions. Without micro curiosity, generalists often fail at the macro level.

To ask ‘why’ relentlessly, a generalist must be ruthlessly curious.

3. Adapt and thrive

By now, startups have found titles for some generalists: Founders’ Associate, Entrepreneur In Residence, or Chief of Staff.

However, anyone carrying this title is not necessarily a generalist. Conversely, anyone not carrying this title could still be a generalist.

Generalism means adapting your role but keeping a big-picture mindset.

When I stepped into Sales Ops or HR, I wasn’t filling gaps – I was broadening my expertise. I could uncover bottlenecks specialists would have missed.

Generalists do whatever matters most. While often pushed into specialization, their value lies in seeing the whole system, not just a part of it.

Generalists fight to be the first arrivers on any scene.

4. Connecting where others can’t

When systems fall apart, it’s often because the connections between parts are frayed.

Generalists see the entire system and connect where specialists can’t. They integrate teams by translating specialized knowledge into a common language.

As a Chief of Staff, I frequently acted as a translator. Whether it was engineering and marketing, or finance and sales – I became an emissary between different kingdoms.

This broad visibility into the org gives generalists access to key decision-making rooms. They help leaders see the full picture, making more nuanced decisions.

More than just problem-solvers, generalists create social glue by building trust between teams. The most cohesive orgs are often bonded through generalism.

Generalists excel at building relationships inside and outside the org.

Generalists seek each other out. A conversation with another Chief Of Stuff can spark solutions you didn’t know you needed.

5. The age of generalists

Choose your specialization. Become an artisan of your craft. Follow down a path you have long chosen for yourself. Ever since industrialization, the common advice was to become ever better at one thing.

Today’s technological advances and startups require generalists who can quickly adapt and weave the webs of future orgs.

Developing adaptive systems depends on communication. Generalists thrive on translating language into context and building trust among teams – skills that remain critical no matter how advanced our tools become.

The world still needs artisans, maybe more than ever before. But the future belongs to those who can see the whole system, adapt constantly, and lean into their curiosity.

The future belongs to generalists.

If you’re willing to explore adjacent themes around technology, startups, and the generalists who drive them, then this blog will be for you. In the future, we’ll also dive into more tactical advice and insights – building on this vision of generalism.